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butane. Review. Alkanes. C n H 2n+2. C 4 H 10. a) ethane b) propane c) butane d) pentane. CH 3. (CH 2 ) . CH 3. 2. Newman projections. butane. 1. 2. 3. 4. 1. 2. 3. 4. staggered. eclipsed. stable. Nomenclature. 1. 2. 1. 3. 7. 3. 1. 3. 5. 7. 4. 6. 4. 2. 4.

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review

butane

Review

Alkanes

CnH2n+2

C4H10

a) ethane

b) propane

c) butane

d) pentane

CH3

(CH2)

CH3

2

newman projections
Newman projections

butane

1

2

3

4

1

2

3

4

staggered

eclipsed

stable

nomenclature
Nomenclature

1

2

1

3

7

3

1

3

5

7

4

6

4

2

4

6

5

2

5

6

7

heptane

heptane

heptane

3

2

branches

4

branches

branches

nomenclature1
Nomenclature

1

2

2-

methyl

methyl

3-

ethyl

3

5

7

4

6

ethyl

4-

propyl

propyl

5-

ethyl

3,5-diethyl

3,5-diethyl

-2-methyl

-4-propyl

heptane

cycloalkanes
Cycloalkanes

linear alkanes

CnH2n+2

branched alkanes

cycloalkanes

closed rings

CnH2n

2

3

cyclo

propane

1

bond angle = 60o

tetrahedral angle = 109o

very unstable

cycloalkanes1
Cycloalkanes

cyclobutane

bond angle = 88o

tetrahedral angle = 109o

unstable

cycloalkanes2
Cycloalkanes

cyclopentane

bond angle = 108o

tetrahedral angle = 109o

stable

cycloalkanes3

geometricisomers

Cycloalkanes

-

-

trans-

1,3-

dichloro

cyclo

butane

cis-

1,3-

dichloro

cyclo

butane

cycloalkanes4
Cycloalkanes

cyclohexane

predicted bond angle = 120o

tetrahedral angle = 109o

stable

cyclohexane
cyclohexane

axial positions

crowded

onlyH

equatorial positions

larger groups

boat conformation

chair conformation

stable

unstable

cyclohexane1
cyclohexane

cis-

1,2-

dimethyl

cyclo

hexane

cis-1,2-dimethylcyclohexane

axial-equatorial

trans-

1,2-dimethylcyclohexane

trans-1,2-dimethylcyclohexane

axial-axial

equatorial-equatorial

optical isomerism
Optical isomerism

Stereocenter

4 different

substituents

C*=

*

*

3-methyl

hexane

bromo

chloro

iodo

methane

*

*

bromo

cyclo

pentane

trans-

1,3-dibromo

cyclopentane

no C*

alkane summary
Alkane Summary

1. Alkanes -sp3 hybridized

2. Relatively unreactive

Substitution with halogens

Combustion

3. Non-polar

IMF = London Dispersion Forces

size

structure

slide14

4. Free rotation around C-C bonds

conformations

5. Non-cyclic alkanes - structural isomers

6. Cyclic alkanes - geometric isomers

cis-, trans-

7. Alkanes -optical isomers

stereocenters

C*